Process for preparing tert-octylamine

A technology of tert-octylamine and tert-octylphenylacetamide, which is applied in the field of preparation of tert-octylamine, can solve problems such as high equipment and operation requirements, no industrial value, and shortened hydrolysis reaction time, achieving important environmental protection significance, Improve the effect of industrial application value and output value

Inactive Publication Date: 2009-06-24
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common defects are: using highly toxic chemicals such as sodium cyanide, a large amount of acid and alkali, harsh hydrolysis conditions, and polluting the environment
Another report of cyanochloride or tert-butyl chloride has no industrial value due to low yield and high cost of raw materials
[0004] Found through literature search to prior art, Chinese patent application number is the patent of CN02113120.1, adopts diisobutene and acetonitrile (or sodium cyanide) reaction in glacial acetic acid to generate N-tert-octylacetamide, then sodium hydroxide A method for preparing tertiary octylamine by aqueous solution hydrolysis, which solves the recovery of acetic acid in the preparation method reported abroad and shortens the hydrolysis reaction time, but needs to be heated in an autoclave to 180-280°C, which requires equipment and operation higher

Method used

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  • Process for preparing tert-octylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 93.2ml of diisobutylene and 57.6ml of phenylacetonitrile into a reaction flask containing 286ml of glacial acetic acid, add 3ml of water, add 50ml of concentrated sulfuric acid dropwise while stirring, and control the temperature in a water bath to not exceed 50°C. After the dropwise addition, the stirring reaction was continued at 40-45°C for 6 hours. Detection, benzyl nitrile has reacted completely.

[0019] The reaction feed liquid was distilled under reduced pressure to collect glacial acetic acid and unreacted diisobutylene, and 500 grams of ice-water mixture was added to the remaining viscous liquid, and a large amount of light brown solids were precipitated. Under vigorous stirring, 5% aqueous sodium hydroxide solution was added to adjust the pH to 5.0. Stand at 0-5°C for 6 hours, filter, wash, and dry to obtain 111.6 g of N-tert-octylphenylacetamide.

[0020] 99 g of N-tert-octylphenylacetamide was dissolved in 400 ml of dimethyl sulfoxide, 600 ml of 0.5N p...

Embodiment 2

[0023] Add 232.9ml of diisobutene and 57.6ml of phenylacetonitrile into a reaction flask containing 428ml of glacial acetic acid, add 3ml of water, add 75ml of concentrated sulfuric acid dropwise under stirring, and control the temperature in a water bath to not exceed 50°C. After the dropwise addition was completed, the stirring reaction was continued at 20-45° C. for 5 hours. Detection, benzyl nitrile has reacted completely.

[0024] The reaction feed liquid is distilled under reduced pressure to collect glacial acetic acid and unreacted diisobutene, and the feed liquid in the distillation bottle is obviously viscous and the distillate speed is slow to stop the distillation under reduced pressure. Add ice-water mixture to the remaining viscous liquid, add 5% sodium hydroxide aqueous solution to adjust pH under vigorous stirring, let stand, filter, wash and dry to obtain 118.3 g of N-tert-octylphenylacetamide.

[0025] Dissolve 99 g of N-tert-octylphenylacetamide in 400 ml o...

Embodiment 3

[0028] Add 116.2ml of diisobutylene and 57.6ml of phenylacetonitrile into a reaction flask containing 400ml of glacial acetic acid, add 3ml of water, add 80ml of concentrated sulfuric acid dropwise under stirring, and control the temperature in a water bath to not exceed 50°C. After the dropwise addition, the stirring reaction was continued at 40-50° C. for 4 hours. Detection, benzyl nitrile has reacted completely.

[0029] The reaction feed liquid is distilled under reduced pressure to collect glacial acetic acid and unreacted diisobutene, and the feed liquid in the distillation bottle is obviously viscous and the distillate speed is slow to stop the distillation under reduced pressure. Add ice-water mixture to the remaining viscous liquid, add 5% sodium hydroxide aqueous solution to adjust pH under vigorous stirring, let stand, filter, wash and dry to obtain 112.8 g of N-tert-octylphenylacetamide.

[0030] Dissolve 99 g of N-tert-octylphenylacetamide in 400 ml of dimethyl s...

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Abstract

The invention discloses a preparation method of tert-octylamine, which belongs to the technical field of chemical industry. The preparation process of the invention is as follows: (1) Using glacial acetic acid as a solvent, diisobutene and phenylacetonitrile are reacted under the action of concentrated sulfuric acid and water to generate N-tert-octyl phenylacetamide; (2) In a suitable solvent system, adding N-tert-octyl Phenylacetamide and acylase, make N-tert-octyl phenylacetamide fully hydrolyzed by acylase, and separate tert-octylamine and phenylacetic acid through distillation and recrystallization. Compared with the existing preparation method of tert-octylamine, the invention can not only improve the yield, but also co-produce phenylacetic acid at the same time, and can significantly improve the comprehensive economic benefit. And the hydrolysis conditions are mild and environmentally friendly.

Description

technical field [0001] The invention relates to a method in the technical field of chemical engineering, in particular to a preparation method of tert-octylamine. technical background [0002] Tertiary octylamine is an important organic intermediate, mainly used in the synthesis of light stabilizer 944 and the manufacture of resins, and also in the fields of metal extraction and pharmaceuticals. It is used as an intermediate in the manufacture of rubber accelerators, pesticides, dyes, and pharmaceuticals. For example, it is used in the production of clavulanic acid, a β-lactamase inhibitor. [0003] Part of the bibliographical reports of the preparation method of tert-octylamine in the prior art, the reaction scheme is basically the same, under the catalysis of concentrated sulfuric acid, diisobutene and acetonitrile (or sodium cyanide) react in glacial acetic acid solution to generate N-tert-octyl acetamide , and then acid or base catalyzed hydrolysis to give tert-octylam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/00C07C209/00C07C211/03
Inventor 张健存陈尧章丽辉彭英丹刘文陆崔大军
Owner SHANGHAI JIAO TONG UNIV
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